Shows / Cheeky Pint
Cheeky Pint
Stripe cofounder John Collison interviews founders, builders, and leaders over a pint.
Episodes
Cheeky PintWhy Sam Altman is against a single superintelligence
Sam Altman, CEO of OpenAI, joins John to break down how models uncovered critical PHP vulnerabilities, why test-time compute unlocks massive agent swarms, and…
Cheeky PintThe airline CEO putting Starlink on every plane
Scott Kirby, CEO of United Airlines, joins John and Ben Thompson to break down the airline business and United’s contrarian bets shaping commercial aviation…
Cheeky PintHow Toto Wolff built the most valuable team in F1
Toto Wolff, Team Principal and Co-Owner of the Mercedes-AMG PETRONAS F1 Team, joins John Collison for a pint to discuss the engineering, management, and…
Cheeky PintThe company building underwater drones for $50,000
Will O'Brien, founder and CEO of Ulysses, joins John and Chris Sacca for a pint to discuss how underwater autonomous robots are scaling up to solve critical…
Cheeky PintMuse Wonder: Zuckerberg and Wang's $100B AI
As Meta scales its AI infrastructure past five gigawatts, Mark Zuckerberg (founder and CEO, Meta) and Alexandr Wang (Chief AI Officer, Meta Superintelligence…
Cheeky PintWhat comes after smartphones, with Snap CEO Evan Spiegel
Snap CEO Evan Spiegel joins John at the pub for a deep dive into Snap's "crucible moment" of 2026: the long-awaited consumer launch of Spectacles. Evan…
Cheeky PintThe economics and trends of the restaurant industry, with Tony Xu of DoorDash
Tony Xu, cofounder and CEO of DoorDash, joins John for a pint to discuss how they won a crowded market by obsessing over retention and the reality of fighting…
Cheeky PintThe world of voice AI, with Mati Staniszewski of ElevenLabs
Mati Staniszewski is the co-founder of ElevenLabs, the research company making audio accessible across languages and voices. He sits down with John to discuss…
Cheeky PintThe history and future of AI at Google, with Sundar Pichai
Sundar Pichai is the CEO of Google and Alphabet. He sits down with John and Elad Gil to discuss Google’s resurgence in the AI race, managing a massive $180…
Cheeky PintCompliance at scale and why TAM is a distraction with Christina Cacioppo of Vanta
Christina Cacioppo, founder and CEO of Vanta, joins the pub to discuss building the future of agentic trust. She explains why compliance has a “vitamin vs…
Cheeky PintThe 20-year journey to fully autonomous cars with Dmitri Dolgov of Waymo
Waymo is now doing nearly 500,000 rides a week across 10 cities. Co-CEO Dmitri Dolgov came to the pub to discuss how they moved from scientific research to…
Cheeky PintCreating prediction markets (and suing the CFTC) with Tarek Mansour and Luana Lopes Lara
Tarek Mansour and Luana Lopes Lara are the co-founders of Kalshi, the first federally regulated prediction market in the US. They sit down with John and Matt…
Cheeky PintBret Taylor of Sierra on AI agents, outcome-based pricing, and the OpenAI board
Bret Taylor, co-founder of Sierra and Chair of the OpenAI board, joins John for a pint to discuss the rapid shift toward an agentic future. In this episode…
Cheeky PintGarrett Langley of Flock Safety on building technology to solve crime
Garrett Langley is the founder and CEO of Flock Safety, a public safety operating system that helps communities and law enforcement eliminate crime. He sits…
Cheeky PintReiner Pope of MatX on accelerating AI with transformer-optimized chips
Reiner Pope is the co-founder and CEO of MatX, designing specialized chips for Large Language Models. A former Google TPU architect, he joins John to discuss…
Cheeky PintStripe’s 2025 annual letter
The internet economy accelerated in 2025. The fastest-growing companies got even faster, agentic commerce and stablecoin payments started to kick into gear…
Cheeky PintRamp founder Eric Glyman on the many ways AI is changing corporate spending
Eric Glyman is the cofounder and CEO of Ramp, the finance automation platform that now powers over 2% of all corporate spend in the US. He sits down with John…
Cheeky PintBen Thompson from Stratechery on AI ads, the end of SaaS, and the future of media
Ben Thompson, the internet’s premier tech analyst, joins John for a wide-ranging conversation on the mechanics of the internet economy. They discuss the…
Cheeky PintElon Musk on Space GPUs, AI, Optimus, and his manufacturing method
John Collison and Dwarkesh Patel sit down with Elon Musk to discuss why the future of AI isn’t on Earth, but in the "always sunny" vacuum of space. Between…
Cheeky PintJulia DeWahl of Antares on building nuclear reactors for the US military
Julia DeWahl is the cofounder of Antares, a company developing nuclear micro-reactors for the US military and critical infrastructure. She sits down with John…
Cheeky PintSatya Nadella describes how lessons from Microsoft’s history apply to today’s boom
Satya Nadella, CEO of Microsoft, sits down with John to discuss the diffusion of AI inside the enterprise. He explains why “all your data at your fingertips”…
Cheeky PintDave Ricks, CEO of Eli Lilly, on GLP-1s and the business of pharma
Dave Ricks, the CEO of Eli Lilly, the world's most valuable pharmaceutical company, sits down with John and Patrick to discuss the complex business of drug…
Cheeky PintStablecoin special: Zach Abrams (Bridge) and Henri Stern (Privy)
Zach Abrams, the CEO and cofounder of Bridge, the leading stablecoin orchestration platform, and Henri Stern, CEO and cofounder of Privy, the leading crypto…
Cheeky PintCasey Handmer of Terraform Industries on solar maximalism, hard tech, and reclaiming the Salton Sea
Description Casey Handmer is the founder of Terraform Industries, who is developing a machine that makes synthetic natural gas from sunlight and air. He joins…
Cheeky PintDan Sundheim of D1 Capital on the art of public market investing
Seasoned public and private investor Dan Sundheim sits down with John to discuss the harrowing GameStop short squeeze, waking up at 3am for the European market…
Cheeky PintHow to build a $16B car company with RJ Scaringe, founder of Rivian
RJ Scaringe, founder and CEO of Rivian, sits down for a cheeky pint with John Collison to discuss what it takes to build a car company from scratch, developing…
Cheeky PintTobi Lütke is still captivated by internet commerce, 20 years later
Shopify founder and CEO Tobi Lütke joins John Collison to discuss the philosophies driving one of the internet’s most foundational companies. Tobi shares his…
Cheeky PintMarc Andreessen and Charlie Songhurst on the past, present, and future of Silicon Valley
Marc Andreessen, cofounder of Netscape and Andreessen Horowitz, sits down for a Cheeky Pint with John Collison and Charlie Songhurst to discuss the history of…
Cheeky PintDes Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
Des Traynor, cofounder of Intercom, sits down for a Cheeky Pint with John Collison to discuss the growth of Fin (Intercom’s AI customer service agent), why…
Cheeky PintAmbrook CEO Mackenzie Burnett on American agriculture, rural resilience, and carrying 50lbs of fresh pork on Amtrak
Mackenzie Burnett joins John Collison to talk about American agriculture, labor and immigration challenges, building rural resilience, ERPs, and the principle…
Cheeky PintZipline CEO Keller Cliffton on air-dropping blood to Rwandan hospitals and getting to 50,000 aircraft per year
Keller Cliffton joins John Collison to talk about Zipline’s journey to 115 million miles flown, the lost art of American airplanes, building 50k drones a year…
Cheeky PintCognition CEO Scott Wu on acquiring Windsurf, AI replacing engineers, and the Moneyball-ification of everything
Scott Wu joins John Collison to talk about Cognition’s AI software engineer, the Moneyball-ification of everything, math competitions with Alexandr Wang in 6th…
Cheeky PintCoinbase CEO Brian Armstrong on bitcoin going to $1 million, electing a pro-crypto Congress, and Jamie Dimon
Brian Armstrong joins John Collison to talk about what’s happening behind the scenes at Coinbase: battling North Korean hackers, war stories from early…
Cheeky PintRobinhood CEO Vlad Tenev on tokenizing private companies, changing the SEC, and Frank Slootman
Vlad Tenev joins John Collison to discuss Bulgarian hyperinflation, Robinhood Banking, details from the GameStop saga—including advice from Marc Benioff, Mark…
Cheeky PintAnthropic CEO Dario Amodei on designing AGI-pilled products, model economics, and 19th-century vitalism
Dario Amodei joins John Collison to talk about Anthropic's growth to ~$5 billion in ARR, how AI models show capitalistic impulses, predictions for an agentic…
Cheeky PintSerial entrepreneur Pieter Levels on building in public and living as a digital nomad
Pieter Levels joins John Collison to discuss building successful online businesses as a digital nomad, thoughts on European accelerationism, and Pieter’s…
Cheeky PintThe Bot Company founder and CEO Kyle Vogt on home robots and why he’ll never sell another company
The Bot Company founder and CEO Kyle Vogt—who also cofounded Twitch and Cruise—joins John Collison to talk about applying AI to home robots, the similarities…
Cheeky PintMeta CFO Susan Li on headcount vs. GPU allocation, “free cash flow” hats, and almost becoming a PM
Susan Li of Meta—the youngest chief financial officer of a Fortune 100 company—joins John Collison to talk about capital allocation, managing investors, and…
Cheeky PintOpenAI cofounder Greg Brockman on the scaling hypothesis and refactoring as a killer AI use case
Greg Brockman—OpenAI cofounder and Stripe's first engineer—joins John Collison to talk about research-driven product development, an early moment he thought…
Cheeky PintCheeky Pint hosted by Stripe cofounder John Collison
John sits down with founders and builders over a pint—Greg Brockman (cofounder of OpenAI), Susan Li (chief financial officer at Meta), Kyle Vogt (founder of…